Mixed chromium containing monoazo dyestuff complexes

ABSTRACT

CHROMIUM CONTAINING MIXED COMPLEXES REPRESENTED BY THE GENERAL FORMULA:   (I)-CR-(II)   WHERE (I) AREPRESENTS THE RESIDUE OF A MONOAZO DYE OF THE GENERAL FORUMULA:   1-HO,2-((2-HO,3-Y,4-X-PHENYL)-N=N-),4-CH3-NAPHTHALENE   WHERE X AND Y ARE EACH HYDROGEN OR CHLORINE ATOMS OR NITRO GROUPS AND (II) IS THE RESIDUE OF A MONOAZO DYE OF THE GENERAL FORMULA:   A-N=N-B   WHERE A REPRESENTS A RADICAL OF AN O-AMINOPHENOL OR O-AMINONAPHTHOL CONTAINING AN -SO3H GROUP AND B REPRESENTS THE RADICAL OF A HYDROXYL CONTAINING COUPLING COMPOUND, FOR EXAMPLE A NAPHTHOL, COUPLING IN A POSITION ORTHO TO THE FUNCTIONAL -OH GROUP.

United States Patent Int. Cl. C09d 435/16; D06p 1/02 US. Cl. 260-145 1Claim ABSTRACT OF THE DISCLOSURE Chromium containing mixed complexesrepresented by the general formula:

(I)Cr(II) where (I) represents the residue of a monoazo dye of thegeneral formula:

where X and Y are each hydrogen or chlorine atoms or nitro groups and(II) is the residue of a monoazo dye of the general formula:

where A represents a radical of an o-aminophenol or o-aminonaphtholcontaining an SO H group and B represents the radical of a hydroxylcontaining coupling compound, for example a naphthol, coupling in aposition ortho to the functional -OH group.

The present invention deals with new chromium con- ,taining mixedcomplexes represented by the general formula:

(I)Cr-(1I) (III) where (I) represents the residue of a monoazo dye ofthe general formula:

where X and Y are each hydrogen or chlorine atoms or nitro groups and(II) is the residue of a monoazo dye of the general formula:

where A represents a radical of an o-aminophenol or o-aminonaphtholcontaining an SO H group and B represents the radical of a hydroxylcontaining coupling compound, for example a naphthol, coupling in aposition ortho to the functional OH group.

The monoazo dyes of Formula I, may be prepared ice in a known manner bycoupling in an alkaline medium. Suitable diazotizable compounds are forexample,

4-ch1oro-1hydroxy-2-amino-benzene, 4,6-dichlorolhydroxy-2-amino-benzene, 4-nitro-1hydroxy-Z-amino-benzene or4,6-dinitr0- 1hydroxy-2-amino-benzene The mixed complexes of Formula IIImay be obtained for example by reacting, in an alkaline aqueous medium achromium complex of an o-hydroxy aliphatic or aromatic carboxylic acid,such as salicylic or tartaric acid, with an equimolecular mixture ofdyestuffs of Formulae I and II. It is also possible for example toreact, in an alkaline aqueous medium, a 1:1 chromium complex of adyestuif of Formula II with a dyestuff of Formula I.

The mixed complexes obtained in this manner are particularly convenientfor dyeing, preferably in a weak organic acid medium, for example inacetic acid medium, animal fibres, such as silk, leather or wool,synthetic fibres based on polyamides or polyurethanes, and also mixedfibres, for example wool-polyamides. The resulting colours are fast torubbing and to wet tests and have excellent fastness to light.

The invention is illustrated by but not limited to the followingexamples in which the amounts used are expressed in parts by weight andthe temperatures in degrees centigrade.

EXAMPLE 1 43.9 parts of [6nitro-4-sulpho-2-hydroxy-naphthalene] l azo 1[2-hydroxy-naphthalene] and 32.3 parts of 5'-nitro-2'-hydroxy-2phenylazo-4- methyl-l-naphthol are mixed in 600 parts of water. Themixture is heated to -95 C. and the pH is adjusted to 10 by the additionof caustic soda. Next 333 parts of a solution of sodium chromosalicylatecontaining 5.2 parts of chromium are added and the mixture is maintainedfor 3 hours at 90-95 C. The mixed chromiumcontaining dyestuff which isobtained is brought down by the addition of 300 parts of sodium chlorideand is dried. This dyestuff dyes wool and polyamides to a black shadewhich has very good general fastness.

EXAMPLE 2' 43.9 parts of a chromium complex of [6nitro-4-sulpho2-hydroxy-naphthalene]- 1 azo 1 [Z-hydroxy-naphthalene]containing one atom of chromium per molecule of the monoazo dye, and32.9 parts of 5'-nitro-2'-hydroxy-2- phenylazo-4-methyl-l-naphthol aremixed in 600 parts of water. The mixture is heated to 90l00 C. and 16.8parts of caustic soda are added so that the pH is maintained at 10-12.The reaction mixture is maintained at 90100 C. until the monoazo dyedisappears. The mixed chromium-containing dyestutf is brought down bythe addition of sodium chloride and is dried. This dyestutf dyes wooland polyamides to a black shade which has very good general fastness.Mixtures of these two fibres show no differences in shade between thefibres.

The following table gives other examples of chromiumcontaining mixedcomplexes prepared from monoazo dyes of Formulae I and '11 according tothe methods of Examples 1 and 2.

Example I II Clour 3 3,5-dinitr0-2-hydroxy-2-pheny1azo-4-methy1-1-[G-nitro-4-sn1pho-2-hydroxy-naphthalene]- 1 azo 1 -[2hydroxy- Greenishblack.

naphthol. naphthalene]. 45-ehloro-2-hydroxy-Z-phenylazo-4-methy1-1-naphtho1.[4-5li1l%)h0-]2-hydlOXY-IlflPhthfilGnQl- 1 azo 1 -[2-hydroxy-naph-Marine blue. a cue 5 5-nitro-2-hydroxy-Z-pheny1azo-4-methyl-l-naphthol.[6-nitro-4-su1pho 2-hydroxy-naphthalene]- 1 azo 2 -[1-hydroxy- Reddishblack.- naphthalene].

We claim: wherein Z represents hydrogen or nitro and B repre- 1. Achromium-containing mixed complex which contains one atom of chromiumbound in complex union with one molecule of a dyestutf of the formula:

OH OH wherein each X and Y represents hydrogen, chlorine or nitro, andwith one molecule of a dyestuff of the formula:

HOGS N=N-B sents the l-hydroxy-Z-naphthyl or 2-hydroxy-1-naphthy1radical.

References Cited UNITED STATES PATENTS 2,906,746 9/1959 Brassel et a1.260145 3,163,634 12/1964 Conrad 260-145 CHARLES E. PARKER, PrimaryExaminer D. M. PAPUGA, Assistant Examiner US. Cl. X.R.

